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New azodyrecins identified by a genome mining-directed reactivity-based screening
Atina Rizkiya Choirunnisa1, Kuga Arima1, Yo Abe1
1Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Beilstein Journal of Organic Chemistry
|September 2, 2022
Summary
Researchers discovered four new azodyrecins from Streptomyces bacteria. They found the double bond in their side chain is key for cytotoxicity and identified the enzyme responsible for their biosynthesis.
Area of Science:
- Natural Product Chemistry
- Microbiology
- Biochemistry
Background:
- Azoxy natural products are rare despite their significant biological activities.
- Aliphatic azoxides represent a largely unexplored class of natural products.
- Streptomyces species are known producers of diverse bioactive secondary metabolites.
Purpose of the Study:
- To identify and characterize novel aliphatic azoxy natural products.
- To investigate the structure-activity relationship of azodyrecins.
- To elucidate the biosynthetic pathway of azodyrecins.
Main Methods:
- Reactivity-based screening targeting azoxy bonds for natural product isolation.
- Spectroscopic analysis for structural elucidation of new compounds.
- In vitro assays to determine biological activity and enzyme function.
Main Results:
- Four new azodyreins (D-G) were isolated from Streptomyces species.
- Cytotoxicity of azodyrecins is dependent on the double bond in the alkyl side chain.
- The S-adenosylmethionine (SAM)-dependent methyltransferase Ady1 was identified as key in azodyrecin biosynthesis.
Conclusions:
- This study expands the known diversity of azoxy natural products.
- The findings highlight the importance of specific structural features for biological activity.
- The identified biosynthetic pathway enables genome-mining for related compounds and future mechanistic studies.
